Amine compound and organic light emitting diode comprising same

ABSTRACT

Provided is a compound of Chemical Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein:
           Ar11 to Ar15 are each independently a substituted or unsubstituted aryl or heteroaryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,   L and L2 to L5 are each independently a direct bond or a substituted or unsubstituted arylene group,   R1 is hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted aryl or heteroaryl group, and is bonded to an adjacent substituent to form a substituted or unsubstituted ring,   r1 is 0 to 8, and when r1 is 2 or more, the R1s are the same as or different from each other, and   n is an integer from 1 to 3, and when n is 2 or 3, the Ls are the same as or different from each other,
 
and an organic light emitting diode comprising the same.

CROSS-REFERENCE TO RELATED APPLICATION(S)

This application is a National Stage Application of InternationalApplication No. PCT/KR2019/004031 filed on Apr. 5, 2019, which claimspriority to and the benefit of Korean Patent Application No.10-2018-0039620 filed in the Korean Intellectual Property Office on Apr.5, 2018, the entire contents of which are incorporated herein byreference.

TECHNICAL FIELD

The present specification relates to an amine compound and an organiclight emitting device including the same.

BACKGROUND

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy by using anorganic material. An organic light emitting device using the organiclight emitting phenomenon usually has a structure including a positiveelectrode, a negative electrode, and an organic material layerinterposed therebetween. Here, the organic material layer has in manycases a multi-layered structure composed of different materials in orderto improve the efficiency and stability of the organic light emittingdevice, and for example, can be composed of a hole injection layer, ahole transport layer, a light emitting layer, an electron transportlayer, an electron injection layer, and the like. In the structure ofthe organic light emitting device, if a voltage is applied between thetwo electrodes, holes are injected from the positive electrode into theorganic material layer and electrons are injected from the negativeelectrode into the organic material layer, and when the injected holesand electrons meet each other, an exciton is formed, and light isemitted when the exciton falls down again to a ground state.

There is a continuous need for developing a new material for theaforementioned organic light emitting device.

BRIEF DESCRIPTION Technical Problem

The present specification provides an amine compound and an organiclight emitting device including the same.

Technical Solution

An exemplary embodiment of the present specification provides a compoundof Chemical Formula 1:

In Chemical Formula 1:

Ar11 to Ar15 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group or a substitutedor unsubstituted heteroaryl group, or are bonded to an adjacentsubstituent to form a substituted or unsubstituted ring;

L and L2 to L5 are the same as or different from each other, and areeach independently a direct bond or a substituted or unsubstitutedarylene group;

R1 is hydrogen, deuterium, a halogen group, a nitrile group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heteroaryl group, and is bonded to an adjacent substituentto form a substituted or unsubstituted ring;

r1 is an integer from 0 to 8, and when r1 is 2 or more, the R1s are thesame as or different from each other; and

n is an integer from 1 to 3, and when n is 2 or 3, the Ls are the sameas or different from each other.

Further, an exemplary embodiment of the present specification providesan organic light emitting device including: a first electrode; a secondelectrode provided to face the first electrode; and an organic materiallayer having one or more layers provided between the first electrode andthe second electrode, in which one or more layers of the organicmaterial layer include the compound of Chemical Formula 1.

Advantageous Effects

A compound according to an exemplary embodiment of the presentspecification can be used as a material for an organic material layer ofan organic light emitting device, and it is possible to improveefficiency, achieve a low driving voltage, and/or improve service lifecharacteristics, in the organic light emitting device by using the same.

BRIEF DESCRIPTION OF DRAWINGS

FIGS. 1 to 4 illustrate an organic light emitting device according toexemplary embodiments of the present specification.

EXPLANATION OF REFERENCE NUMERALS AND SYMBOLS

-   -   1: Substrate    -   2: Positive electrode    -   3: Light emitting layer    -   4: Negative electrode    -   5: Hole injection layer    -   6: Hole transport layer    -   7: Electron injection and transport layer    -   8: Electron blocking layer    -   9: Hole blocking layer

DETAILED DESCRIPTION

Hereinafter, the present specification will be described in more detail.

An exemplary embodiment of the present specification provides thecompound of Chemical Formula 1.

The compound of Chemical Formula 1 has a structure in which twoarylamine groups or arylheteroarylamine groups are linked to a corestructure of benzocarbazole. When the compound of Chemical Formula 1 isused as a dopant of a blue light emitting layer, the color purity of adevice is improved, and long service life, high efficiency, and lowvoltage characteristics are exhibited.

When one part “includes” one constituent element in the presentspecification, unless otherwise specifically described, this does notmean that another constituent element is excluded, but means thatanother constituent element can be further included.

When one member is disposed “on” another member in the presentspecification, this includes not only a case where the one member isbrought into contact with another member, but also a case where stillanother member is present between the two members.

In the present specification,

or * means a moiety to be linked.

Examples of the substituents in the present specification will bedescribed below, but are not limited thereto.

The term “substitution” means that a hydrogen atom bonded to a carbonatom of a compound is changed into another substituent, and a positionto be substituted is not limited as long as the position is a positionat which the hydrogen atom is substituted, that is, a position at whichthe substituent can be substituted, and when two or more aresubstituted, the two or more substituents can be the same as ordifferent from each other.

In the present specification, the term “substituted or unsubstituted”means being substituted with one or two or more substituents selectedfrom the group consisting of hydrogen, deuterium, a halogen group, anitrile group, a silyl group, an alkyl group, a cycloalkyl group, ahaloalkyl group, an alkoxy group, a haloalkoxy group, an aryloxy group,an aryl group, and a heterocyclic group, being substituted with asubstituent to which two or more substituents among the exemplifiedsubstituents are linked, or having no substituent. For example, “thesubstituent to which two or more substituents are linked” can be an arylgroup substituted with an aryl group, an aryl group substituted with aheteroaryl group, a heterocyclic group substituted with an aryl group,an aryl group substituted with an alkyl group, and the like.

In the present specification, the case where two or more substituentsare linked means that hydrogen of any one substituent is linked toanother substituent. For example, an isopropyl group can be linked to aphenyl group to become a substituent of

In the present specification, the case where three substituents arelinked includes not only a case where (Substituent 1)-(Substituent2)-(Substituent 3) are consecutively linked to one another, but also acase where (Substituent 2) and (Substituent 3) are linked to(Substituent 1). For example, two phenyl groups can be linked to anisopropyl group to become a substituent of

The same also applies to the case where four or more substituents arelinked.

In the present specification, a halogen group can be F, Cl, I, and thelike, and is preferably F.

In the present specification, a silyl group can be an alkyl silyl groupor an aryl silyl group. The silyl group can be SiRaRbRc, and Ra to Rccan be hydrogen, an alkyl group, or an aryl group.

In the present specification, an alkyl group can be straight-chained orbranched, and the number of carbon atoms thereof is not particularlylimited, but is preferably 1 to 30; 1 to 10; or 1 to 5. Specificexamples thereof include methyl, ethyl, propyl, n-propyl, isopropyl,butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl,1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl,3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl,cyclopentyl-methyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl,1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl,2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl,2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are notlimited thereto.

In the present specification, a cycloalkyl group is not particularlylimited, but has preferably 3 to 30 carbon atoms; or 3 to 13 carbonatoms, and specific examples thereof include cyclopropyl, cyclobutyl,cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl,cyclooctyl, and the like, but are not limited thereto.

In the present specification, a haloalkyl group can be straight-chainedor branched, and refers to a group in which hydrogen of theabove-described alkyl group is substituted with one or two or morehalogen groups. The number of carbon atoms thereof is not particularlylimited, but is preferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5. Thedescription on the above-described alkyl group can be applied to thealkyl group. Specific examples of the haloalkyl group include afluoromethyl group, a difluoro-methyl group, a trifluoromethyl group, achloromethyl group, a dichloromethyl group, a trichloromethyl group, abromomethyl group, a dibromomethyl group, a tribromomethyl group, andthe like, but are not limited thereto.

In the present specification, an alkoxy group can be straight-chained,branched, or cyclic. The number of carbon atoms of the alkoxy group isnot particularly limited, but is preferably 1 to 30. Specific examplesthereof include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy,n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethyl-butyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, andthe like, but are not limited thereto.

In the present specification, a haloalkoxy group is a group in which ahaloalkyl group is linked to an oxygen atom, and the description on theabove-described haloalkyl group can be applied to the haloalkyl group.The number of carbon atoms thereof is not particularly limited, but ispreferably 1 to 30; 1 to 20; 1 to 10; or 1 to 5.

In the present specification, an aryl group is not particularly limited,but has preferably 6 to 30 carbon atoms, and the aryl group can bemonocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbonatoms thereof is not particularly limited, but is preferably 6 to 30.Specific examples of the monocyclic aryl group include a phenyl group, abiphenyl group, a terphenyl group, and the like, but are not limitedthereto.

When the aryl group is a polycyclic aryl group, the number of carbonatoms thereof is not particularly limited, but is preferably 10 to 30.Specific examples of the polycyclic aryl group include a naphthyl group,an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenylgroup, a phenalenyl group, a perylenyl group, a chrysenyl group, afluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group can be substituted,and adjacent substituents can be bonded to each other to form a ring.

When the fluorenyl group is substituted, the substituent can be

and the like. However, the substituent is not limited thereto.

In the present specification, the aryl group in the aryloxy group, theN-arylalkylamine group, and the N-arylheteroarylamine group is the sameas the above-described examples of the aryl group. Specific examples ofthe aryloxy group include a phenoxy group, a p-tolyloxy group, anm-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxygroup, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxygroup, and the like.

In the present specification, a heteroaryl group includes one or moreatoms other than carbon, that is, one or more heteroatoms, andspecifically, the heteroatom can include one or more atoms selected fromthe group consisting of O, N, Se, S, and the like. The number of carbonatoms thereof is not particularly limited, but is preferably 2 to 30,and the heteroaryl group can be monocyclic or polycyclic. Examples of aheterocyclic group include a thiophene group, a furan group, a pyrrolegroup, an imidazole group, a triazole group, an oxazole group, anoxadiazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group,a triazinyl group, a triazole group, an acridyl group, a pyridazinylgroup, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, aquinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, apyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinylgroup, an indolyl group, a carbazole group, a benzoxazole group, abenzoimidazole group, a benzothiazole group, a benzocarbazole group, adibenzopyrrole group, an indole group, a benzothiophene group, adibenzothiophene group, a benzofuran group, a benzoquinolyl group, abenzonaphthothiophene group, a benzonaphthofuran group, aphenanthrolinyl group (phenanthroline), a thiazole group, an isoxazolegroup, an oxadiazole group, a thiadiazole group, a benzothiazole group,a phenoxazine group, a phenothiazine group, a dibenzofuran group, andthe like, but are not limited thereto.

In the present specification, the above-described examples of the arylgroup can be applied to an arylene group except for a divalent arylenegroup.

In the present specification, the above-described examples of theheteroaryl group can be applied to a heteroarylene group except for adivalent heteroarylene group.

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and are eachindependently selected from a direct bond, phenylene, biphenylene,terphenylene, quaterphenylene, naphthylene, anthracenylene, fluorenylenewhich is unsubstituted or substituted with alkyl or aryl,phenanthrenylene, pyrenylene, and triphenylylene.

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and can be eachindependently selected from a direct bond or the following structuralformulae:

R and R′ are an alkyl group or an aryl group. For example, R and R′ area methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and can be eachindependently selected from a direct bond or the following structuralformulae:

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and are eachindependently a direct bond, phenylene, or a biphenylene group.

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and are eachindependently a direct bond, or phenylene.

According to an exemplary embodiment of the present specification, L andL2 to L5 are the same as or different from each other, and are eachindependently a direct bond, p-phenylene, or m-phenylene.

According to an exemplary embodiment of the present specification, L andL2 to L5 are a direct bond.

According to an exemplary embodiment of the present specification, L isa direct bond.

According to an exemplary embodiment of the present specification, L2 toL5 are the same as or different from each other, and are eachindependently a direct bond, or phenylene.

According to an exemplary embodiment of the present specification, Ar11to Ar14 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar11to Ar14 are the same as or different from each other, and are eachindependently a substituted or unsubstituted aryl group having 6 to 30carbon atoms; or a substituted or unsubstituted heteroaryl group having2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar11to Ar14 are the same as or different from each other, and are eachindependently an aryl group which is unsubstituted or substituted withone substituent selected from the group consisting of deuterium, ahalogen group, a nitrile group, an alkyl group, a haloalkyl group, analkoxy group, a haloalkoxy group, a silyl group, and a cycloalkyl group,or a substituent to which two or more substituents selected from thegroup are linked; or a heteroaryl group which is unsubstituted orsubstituted with one substituent selected from the group consisting ofdeuterium, a halogen group, a nitrile group, an alkyl group, a haloalkylgroup, an alkoxy group, a haloalkoxy group, a silyl group, and acycloalkyl group, or a substituent to which two or more substituentsselected from the group are linked.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is an aryl group, the aryl group is a phenyl group, anaphthyl group, a biphenyl group, a fluorenyl group, or a benzofluorenylgroup.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is a heteroaryl group, the heteroaryl group is adibenzofuran group, a naphthobenzofuran group, a dibenzothiophene group,or a naphthobenzothiophene group.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is a substituted aryl group, the substituent of the arylgroup is deuterium, a halogen group, a nitrile group, an alkyl grouphaving 1 to 5 carbon atoms, which is unsubstituted or substituted withdeuterium, a haloalkyl group having 1 to 5 carbon atoms, an alkoxy grouphaving 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbonatoms, a silyl group having 3 to 20 carbon atoms, or a cycloalkyl grouphaving 3 to 20 carbon atoms.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is a substituted aryl group, the substituent of the arylgroup is deuterium, a halogen group, a nitrile group, a methyl group, anethyl group, a propyl group, an isopropyl group, a t-butyl group, CD₃, atrifluoromethyl group, a methoxy group, an ethoxy group, OCF₃, atrimethylsilyl group, a triphenylsilyl group, or a cyclohexyl group.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is a substituted heteroaryl group, the substituent of theheteroaryl group is deuterium, a halogen group, a nitrile group, analkyl group having 1 to 5 carbon atoms, which is unsubstituted orsubstituted with deuterium, a haloalkyl group having 1 to 5 carbonatoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy grouphaving 1 to 5 carbon atoms, a silyl group having 3 to 20 carbon atoms, acycloalkyl group having 3 to 20 carbon atoms, or an aryl group having 6to 20 carbon atoms, which is unsubstituted or substituted withdeuterium.

In an exemplary embodiment of the present specification, when any one ofAr11 to Ar14 is a substituted heteroaryl group, the substituent of theheteroaryl group is deuterium, a halogen group, a nitrile group, amethyl group, an ethyl group, a propyl group, an isopropyl group, at-butyl group, CD₃, a trifluoromethyl group, a methoxy group, an ethoxygroup, OCF₃, a trimethylsilyl group, a triphenylsilyl group, a phenylgroup, a biphenyl group, a naphthyl group, a terphenyl group, a phenylgroup which is substituted with deuterium, a biphenyl group which issubstituted with deuterium, a naphthyl group which is substituted withdeuterium, or a terphenyl group which is substituted with deuterium.

In an exemplary embodiment of the present specification, Ar11 to Ar14are the same as or different from each other, and are each independentlya phenyl group which is unsubstituted or substituted with deuterium, ahalogen group, a nitrile group, a methyl group, an ethyl group, a propylgroup, an isopropyl group, a t-butyl group, CD₃, a trifluoromethylgroup, OCF₃, a methoxy group, an ethoxy group, a trimethylsilyl group, atriphenylsilyl group, or a cyclohexyl group; a biphenyl group which isunsubstituted or substituted with deuterium, a halogen group, a nitrilegroup, a methyl group, an ethyl group, a propyl group, an isopropylgroup, a t-butyl group, CD₃, a trifluoromethyl group, a methoxy group,an ethoxy group, OCF₃, a trimethylsilyl group, a triphenylsilyl group,or a cyclohexyl group; a naphthyl group which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, a methylgroup, an ethyl group, a propyl group, an isopropyl group, a t-butylgroup, CD₃, a trifluoromethyl group, a methoxy group, an ethoxy group,OCF₃, a trimethylsilyl group, a triphenylsilyl group, or a cyclohexylgroup; a fluorenyl group which is unsubstituted or substituted withdeuterium, a halogen group, a nitrile group, a methyl group, an ethylgroup, a propyl group, an isopropyl group, a t-butyl group, CD₃, atrifluoromethyl group, a methoxy group, an ethoxy group, OCF₃, atrimethylsilyl group, a triphenylsilyl group, or a cyclohexyl group; abenzofluorenyl group which is unsubstituted or substituted withdeuterium, a halogen group, a nitrile group, a methyl group, an ethylgroup, a propyl group, an isopropyl group, a t-butyl group, CD₃, atrifluoromethyl group, a methoxy group, an ethoxy group, OCF₃, atrimethylsilyl group, a triphenylsilyl group, or a cyclohexyl group; adibenzofuran group which is unsubstituted or substituted with deuterium,a halogen group, a nitrile group, a methyl group, an ethyl group, apropyl group, an isopropyl group, a t-butyl group, CD₃, atrifluoromethyl group, a methoxy group, an ethoxy group, OCF₃, atrimethylsilyl group, a triphenylsilyl group, a phenyl group, a biphenylgroup, a naphthyl group, or a phenyl group which is substituted withdeuterium; a naphthobenzofuran group which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, a methylgroup, an ethyl group, a propyl group, an isopropyl group, a t-butylgroup, CD₃, a trifluoromethyl group, a methoxy group, an ethoxy group,OCF₃, a trimethylsilyl group, a triphenylsilyl group, or a cyclohexylgroup; a dibenzothiophene group which is unsubstituted or substitutedwith deuterium, a halogen group, a nitrile group, a methyl group, anethyl group, a propyl group, an isopropyl group, a t-butyl group, CD₃, atrifluoromethyl group, a methoxy group, an ethoxy group, OCF₃, atrimethylsilyl group, a triphenylsilyl group, a phenyl group, a biphenylgroup, a naphthyl group, or a phenyl group which is substituted withdeuterium; or a naphthobenzothiophene group which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, a methylgroup, an ethyl group, a propyl group, an isopropyl group, a t-butylgroup, CD₃, a trifluoromethyl group, a methoxy group, an ethoxy group,OCF₃, a trimethylsilyl group, a triphenylsilyl group, or a cyclohexylgroup.

In an exemplary embodiment of the present specification, Ar11 to Ar14are the same as or different from each other, and are each independentlya phenyl group which is unsubstituted or substituted with deuterium, ahalogen group, a nitrile group, a methyl group, an isopropyl group, at-butyl group, CD₃, a trifluoromethyl group, OCF₃, a methoxy group, or atrimethylsilyl group; a biphenyl group; a naphthyl group; adimethylfluorenyl group; a dimethylbenzofluorenyl group; a dibenzofurangroup which is unsubstituted or substituted with deuterium, a methylgroup, an isopropyl group, a t-butyl group, CD₃, a trimethylsilyl group,a phenyl group, or a phenyl group which is substituted with deuterium; anaphthobenzofuran group; a dibenzothiophene group which is unsubstitutedor substituted with deuterium, a methyl group, an isopropyl group, at-butyl group, CD₃, a trimethylsilyl group, a phenyl group, or a phenylgroup which is substituted with deuterium; or a naphthobenzothiophenegroup.

According to an exemplary embodiment of the present specification,—N(-L2-Ar11) (-L3-Ar12) and —N(-L4-Ar13) (-L5-Ar14) of Chemical Formula1 are the same as each other.

According to an exemplary embodiment of the present specification,-(L)n-Ar15 in Chemical Formula 1 is a phenyl group which isunsubstituted or substituted with deuterium, a halogen group, a nitrilegroup, an alkyl group which is unsubstituted or substituted withdeuterium, an alkoxy group, or a silyl group; or a biphenyl group whichis unsubstituted or substituted with deuterium, a halogen group, anitrile group, an alkyl group which is unsubstituted or substituted withdeuterium, an alkoxy group, or a silyl group.

In an exemplary embodiment of the present specification, Ar15 is asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heteroaryl group, or is bonded to an adjacent group toform a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar15 is bonedto adjacent R1 to form a substituted or unsubstituted aromatichydrocarbon ring.

In an exemplary embodiment of the present specification, Ar15 is bondedto adjacent R1 to form a substituted or unsubstituted benzene ring or asubstituted or unsubstituted naphthalene ring.

In an exemplary embodiment of the present specification, Ar15 is bondedto adjacent R1 to form a benzene ring which is unsubstituted orsubstituted with one substituent selected from the group consisting ofdeuterium, a halogen group, a nitrile group, an alkyl group, a haloalkylgroup, an alkoxy group, a silyl group, and a cycloalkyl group, or asubstituent to which two or more substituents selected from the groupare linked; or a naphthalene ring which is unsubstituted or substitutedwith one substituent selected from the group consisting of deuterium, ahalogen group, a nitrile group, an alkyl group, a haloalkyl group, analkoxy group, a silyl group, and a cycloalkyl group, or a substituent towhich two or more substituents selected from the group are linked.

In an exemplary embodiment of the present specification, Ar15 is bondedto adjacent R1 to form a benzene ring which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, a methylgroup, an isopropyl group, a t-butyl group, a methoxy group, CD3, aphenyl group, a phenyl group which is substituted with deuterium, aphenyl group which is substituted with a halogen group, a phenyl groupwhich is substituted with a nitrile group, or a phenyl group which issubstituted with a methyl group; or a naphthalene ring.

In an exemplary embodiment of the present specification, Ar15 is asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar15is a substituted or unsubstituted aryl group having 6 to 30 carbonatoms.

In an exemplary embodiment of the present specification, Ar15 is asubstituted or unsubstituted phenyl group, a substituted orunsubstituted biphenyl group, or a substituted or unsubstituted naphthylgroup.

According to an exemplary embodiment of the present specification, Ar15is an aryl group which is unsubstituted or substituted with onesubstituent selected from the group consisting of deuterium, a halogengroup, a nitrile group, an alkyl group, a haloalkyl group, an alkoxygroup, a silyl group, and a cycloalkyl group, or a substituent to whichtwo or more substituents selected from the group are linked.

In an exemplary embodiment of the present specification, Ar15 is aphenyl group which is unsubstituted or substituted with deuterium, ahalogen group, a nitrile group, a methyl group, an ethyl group, a propylgroup, an isopropyl group, a t-butyl group, CD₃, a trifluoromethylgroup, a methoxy group, an ethoxy group, a trimethylsilyl group, atriphenylsilyl group, or a cyclohexyl group; a biphenyl group; or anaphthyl group.

In an exemplary embodiment of the present specification, R1 is hydrogenor deuterium, or is bonded to adjacent Ar15 to form a substituted orunsubstituted ring.

In an exemplary embodiment of the present specification, R1 is hydrogenor deuterium, or is bonded to adjacent Ar15 to form a substituted orunsubstituted benzene ring or a substituted or unsubstituted naphthalenering.

In an exemplary embodiment of the present specification, r1 is 0.

In an exemplary embodiment of the present specification, r1 is 1.

In an exemplary embodiment of the present specification, ChemicalFormula 1 is Chemical Formula 2:

In Chemical Formula 2, the definitions of Ar11 to Ar15, L, L2 to L5, R1,r1, and n are the same as those defined in Chemical Formula 1.

In an exemplary embodiment of the present specification, ChemicalFormula 1 is any one of the following Chemical Formulae 301 to 303:

In Chemical Formulae 301 to 303:

the definitions of L2 to L5 and Ar11 to Ar14 are the same as thosedefined in Chemical Formula 1;

Ar21 is a substituted or unsubstituted aryl group or a substituted orunsubstituted heteroaryl group;

R21 and R22 are the same as or different from each other, and are eachindependently hydrogen, deuterium, a halogen group, a nitrile group, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedhaloalkyl group, a substituted or unsubstituted silyl group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted cycloalkyl group, a substituted or unsubstituted arylgroup, or a substituted or unsubstituted heteroaryl group;

k1 and k2 are 0 or 1;

r21 and r22 are an integer from 0 to 6;

when r21 is 2 or more, the R21s are the same as or different from eachother; and

when r22 is 2 or more, the R22s are the same as or different from eachother.

In an exemplary embodiment of the present specification, when k1 or k2is 1, a naphthalene ring is fused to benzocarbazole.

In an exemplary embodiment of the present specification, R21 and R22 arethe same as or different from each other, and are each independently onesubstituent selected from the group consisting of deuterium, a halogengroup, a nitrile group, an alkyl group, a haloalkyl group, an alkoxygroup, a silyl group, and a cycloalkyl group, or a substituent to whichtwo or more substituents selected from the group are linked.

In an exemplary embodiment of the present specification, R21 and R22 arethe same as or different from each other, and are each independentlydeuterium, a halogen group, a nitrile group, a methyl group, anisopropyl group, a t-butyl group, a methoxy group, CD₃, a phenyl group,a phenyl group which is substituted with deuterium, a phenyl group whichis substituted with a halogen group, a phenyl group which is substitutedwith a nitrile group, or a phenyl group which is substituted with amethyl group.

In an exemplary embodiment of the present specification, ChemicalFormula 301 is Chemical Formula 401:

In Chemical Formula 401, definitions of Ar21, L2 to L5, and Ar11 to Ar14are the same as those defined in Chemical Formula 301.

In an exemplary embodiment of the present specification, ChemicalFormula 302 is Chemical Formula 402:

In Chemical Formula 402, the definitions of R21, r21, k1, L2 to L5, andAr11 to Ar14 are the same as those defined in Chemical Formula 302.

In an exemplary embodiment of the present specification, ChemicalFormula 303 is Chemical Formula 403:

In Chemical Formula 403, definitions of R22, r22, k2, L2 to L5, and Ar11to Ar14 are the same as those defined in Chemical Formula 303.

According to an exemplary embodiment of the present specification,Chemical Formula 1 can be any one compound selected from among thefollowing compounds:

According to an exemplary embodiment of the present specification, afull width at half-maximum of the compound of Chemical Formula 1 is 40nm or less. More preferably, the full width at half-maximum is 30 nm orless. When the full width at half-maximum is within the above range, thecolor purity of blue light emission is improved.

The fluorescence intensity and the maximum emission peak can be measuredat room temperature (300 K) by dissolving a compound to be measured at aconcentration of 1 μM in toluene as a solvent to prepare a sample formeasuring fluorescence, putting the sample solution into a quartz cell,and then using a fluorescence measurement apparatus (JASCO FP-8600fluorescence spectrophotometer). In this case, in the fluorescencespectrum, the x axis is the wavelength (λ, unit: nm), the y axis is thelight emission degree, and a spread width of a peak at a height that is½ of the height of the maximum emission peak refers to a full width athalf-maximum.

The compound according to an exemplary embodiment of the presentspecification can be prepared by a preparation method described below.If necessary, a substituent can be added or excluded, and a position ofthe substituent can be changed. Further, a starting material, areactant, reaction conditions, and the like can be changed based on thetechnology known in the art.

For example, a core structure of the compound of Chemical Formula 1 canbe prepared as in the following General Reaction Schemes 1 to 3. Thesubstituent can be bonded by a method known in the art, and the kind orposition of the substituent or the number of substituents can be changedaccording to the technology known in the art. The substituent can bebonded as in the following General Reaction Schemes 1 to 3, but thebonding method is not limited thereto.

In General Reaction Schemes 1 to 3, the definitions of Ar11 to Ar15 arethe same as those defined in Formula 1. In General Reaction Schemes 1 to3, L and L2 to L5 are not represented, but when reactants in which L andL2 to L5 are substituted are used, a desired compound can be obtained.

An exemplary embodiment of the present specification provides an organiclight emitting device including: a first electrode; a second electrodeprovided to face the first electrode; and an organic material layerhaving one or more layers provided between the first electrode and thesecond electrode, in which one or more layers of the organic materiallayer include the above-described compound.

According to an exemplary embodiment of the present specification, theorganic material layer of the organic light emitting device of thepresent specification can be composed of a mono-layer structure, but canbe composed of a multi-layer structure in which two or more organicmaterial layers are stacked. For example, the organic light emittingdevice of the present invention can have a structure including a holeinjection layer, a hole transport layer, an electron blocking layer, alight emitting layer, a hole blocking layer, an electron transportlayer, an electron injection layer, and the like, as organic materiallayers. However, the structure of the organic light emitting device isnot limited thereto, and can include fewer or more organic layers.

In the present specification, the ‘layer’ has a meaning compatible witha ‘film’ usually used in the art, and means a coating covering a targetregion. The size of the ‘layer’ is not limited, and the sizes of therespective ‘layers’ can be the same as or different from one another. Inan exemplary embodiment, the size of the ‘layer’ can be the same as thatof the entire device, can correspond to the size of a specificfunctional region, and can also be as small as a single sub-pixel.

In the present specification, the meaning that a specific A material isincluded in a B layer includes both i) the fact that one or more Amaterials are included in one B layer and ii) the fact that the B layeris composed of one or more layers, and the A material is included in oneor more layers of the multi-layered B layers.

In the present specification, the meaning that a specific A material isincluded in a C layer or a D layer includes all of i) the fact that theA material is included in one or more layers of the C layer having oneor more layers, ii) the fact that the A material is included in one ormore layers of the D layer having one or more layers, and iii) the factthat the A material is included in each of the C layer having one ormore layers and the D layer having one or more layers.

For example, the structure of the organic light emitting device of thepresent specification can have structures illustrated in FIGS. 1 to 4,but is not limited thereto.

FIG. 1 exemplifies the structure of an organic light emitting device inwhich a positive electrode 2, a light emitting layer 3, and a negativeelectrode 4 are sequentially stacked on a substrate 1. FIG. 1 is anexemplified structure of the organic light emitting device according toan exemplary embodiment of the present specification, and can furtherinclude other organic material layers. In the structure described above,the compound of Chemical Formula 1 can be included in the light emittinglayer.

FIG. 2 exemplifies the structure of an organic light emitting device inwhich a positive electrode 2, a hole injection layer 5, a hole transportlayer 6, a light emitting layer 3, an electron injection and transportlayer 7, and a negative electrode 4 are sequentially stacked on asubstrate 1. FIG. 2 is an exemplified structure according to exemplaryembodiments of the present specification, and can further include otherorganic material layers. Here, the compound of Chemical Formula 1 can beincluded in the hole injection layer, the hole transport layer, thelight emitting layer, or the electron injection and transport layer.

FIG. 3 exemplifies a structure of an organic light emitting device inwhich a positive electrode 2, a hole injection layer 5, a hole transportlayer 6, an electron blocking layer 8, a light emitting layer 3, anelectron injection and transport layer 7, and a negative electrode 4 aresequentially stacked on a substrate 1. FIG. 3 is an exemplifiedstructure according to exemplary embodiments of the presentspecification, and can further include other organic material layers.Here, the compound of Chemical Formula 1 can be included in the holeinjection layer, the hole transport layer, the electron blocking layer,the light emitting layer, or the electron injection and transport layer.

FIG. 4 exemplifies a structure of an organic light emitting device inwhich a positive electrode 2, a hole injection layer 5, a hole transportlayer 6, an electron blocking layer 8, a light emitting layer 3, a holeblocking layer 9, an electron injection and transport layer 7, and anegative electrode 4 are sequentially stacked on a substrate 1. FIG. 4is an exemplified structure according to exemplary embodiments of thepresent specification, and can further include other organic materiallayers. Here, the compound of Chemical Formula 1 can be included in thehole injection layer, the hole transport layer, the electron blockinglayer, the light emitting layer, the hole blocking layer, or theelectron injection and transport layer.

According to an exemplary embodiment of the present specification, theorganic material layer includes a hole injection layer, a hole transportlayer, or an electron blocking layer, and the hole injection layer, thehole transport layer, or the electron blocking layer includes thecompound of Chemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the compound of Chemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer includes a light emitting layer, and the lightemitting layer includes the compound of Chemical Formula 1 as a dopantof the light emitting layer.

The organic light emitting device according to an exemplary embodimentof the present specification includes a light emitting layer, and thelight emitting layer includes the compound of Chemical Formula 1 and acompound of Chemical Formula H:

In Chemical Formula H:

L21 and L22 are the same as or different from each other, and are eachindependently a direct bond, a substituted or unsubstituted arylenegroup, or a substituted or unsubstituted heteroarylene group;

R31 to R38 are the same as or different from each other, and are eachindependently hydrogen, deuterium, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted silyl group, a substituted or unsubstituted phosphineoxide group, a substituted or unsubstituted aryl group, or a substitutedor unsubstituted heteroaryl group; and

Ar101 and Ar102 are the same as or different from each other, and areeach independently a substituted or unsubstituted aryl group or asubstituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, L21 and L22 arethe same as or different from each other, and are each independently adirect bond, a substituted or unsubstituted arylene group having 6 to 30carbon atoms, or a substituted or unsubstituted heteroarylene grouphaving 2 to 30 carbon atoms and including N, O, or S.

In an exemplary embodiment of the present specification, L21 and L22 arethe same as or different from each other, and are each independently adirect bond, a substituted or unsubstituted phenylene group, asubstituted or unsubstituted naphthylene group, or a substituted orunsubstituted thiophenylene group.

In an exemplary embodiment of the present specification, Ar101 and Ar102are the same as or different from each other, and are each independentlya substituted or unsubstituted aryl group having 6 to 50 carbon atoms ora substituted or unsubstituted heteroaryl group having 2 to 50 carbonatoms.

In an exemplary embodiment of the present specification, Ar101 and Ar102are the same as or different from each other, and are each independentlya substituted or unsubstituted monocyclic to tetracyclic aryl group or asubstituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

In an exemplary embodiment of the present specification, Ar101 and Ar102are the same as or different from each other, and are each independentlya substituted or unsubstituted phenyl group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted terphenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted anthracene group, a substituted or unsubstitutedphenanthryl group, a substituted or unsubstituted phenalene group, asubstituted or unsubstituted fluorenyl group, a substituted orunsubstituted benzofluorenyl group, a substituted or unsubstituted furangroup, a substituted or unsubstituted thiophene group, a substituted orunsubstituted dibenzofuran group, a substituted or unsubstitutednaphthobenzofuran group, a substituted or unsubstituted dibenzothiophenegroup, or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, R31 to R38 arehydrogen.

In an exemplary embodiment of the present specification, the compound ofChemical Formula H is any one compound selected from the followingcompounds:

The organic light emitting device according to an exemplary embodimentof the present specification includes a light emitting layer, and thelight emitting layer includes the compound of Chemical Formula 1 as adopant of the light emitting layer, and includes the compound ofChemical Formula H as a host of the light emitting layer.

In an exemplary embodiment of the present specification, the content ofthe compound of Chemical Formula 1 is 0.01 part by weight to 30 parts byweight; 0.1 part by weight to 20 parts by weight; or 0.5 part by weightto 10 parts by weight, based on 100 parts by weight of the compound ofChemical Formula H.

In an exemplary embodiment of the present specification, the lightemitting layer can further include one host material in addition to thecompound of Chemical Formula H. In this case, examples of the furtherincluded host material (mixed host compound) include a fused aromaticring derivative, a hetero ring-containing compound, or the like.Specific examples of the fused aromatic ring derivative include ananthracene derivative, a pyrene derivative, a naphthalene derivative, apentacene derivative, a phenanthrene compound, a fluoranthene compound,and the like, and specific examples of the hetero ring-containingcompound include a dibenzofuran derivative, a ladder-type furancompound, a pyrimidine derivative, and the like, but the examples arenot limited thereto.

A weight ratio of the compound of Chemical Formula H to the mixed hostcompound is 95:5 to 5:95, and more preferably 30:70 to 70:30.

In an exemplary embodiment of the present specification, the lightemitting layer includes one or two or more compounds of Chemical FormulaH.

In an exemplary embodiment of the present specification, the lightemitting layer including the compound of Chemical Formula 1 and thecompound of Chemical Formula H takes on a blue color.

The organic light emitting device according to an exemplary embodimentof the present specification includes a light emitting layer having twoor more layers, and at least one of the light emitting layer having twoor more layers includes the compound of Chemical Formula 1 and thecompound of Chemical Formula H. The light emitting layer including thecompound of Chemical Formula 1 and the compound of Chemical Formula Htakes on a blue color, and a light emitting layer which does not includethe compound of Chemical Formula 1 and the compound of Chemical FormulaH can include a blue, red, or green light emitting compound known in theart.

According to an exemplary embodiment of the present specification, theorganic material layer includes a hole blocking layer, an electrontransport layer, an electron injection layer, or an electron injectionand transport layer, and the hole blocking layer, the electron transportlayer, the electron injection layer, or the electron injection andtransport layer includes the compound of Chemical Formula 1.

According to an exemplary embodiment of the present specification, theorganic material layer can further include one or more layers selectedfrom the group consisting of a hole injection layer, a hole transportlayer, an electron blocking layer, a hole blocking layer, an electrontransport layer, and an electron injection layer.

The organic light emitting device of the present specification can bemanufactured by the materials and methods known in the art, except thatone or more layers of the organic material layer include the compound ofthe present specification, that is, the compound of Chemical Formula 1.

When the organic light emitting device includes a plurality of organicmaterial layers, the organic material layers can be formed of the samematerial or different materials.

For example, the organic light emitting device of the presentspecification can be manufactured by sequentially stacking a firstelectrode, an organic material layer, and a second electrode on asubstrate. In this case, the organic light emitting device can bemanufactured by depositing a metal or a metal oxide having conductivity,or an alloy thereof on a substrate to form a first electrode, forming anorganic material layer including a hole injection layer, a holetransport layer, a light emitting layer, and an electron transport layerthereon, and then depositing a material, which can be used as a secondelectrode, thereon, by using a physical vapor deposition (PVD) methodsuch as sputtering or e-beam evaporation. In addition to the methoddescribed above, an organic light emitting device can be made bysequentially depositing a second electrode material, an organic materiallayer, and a first electrode material on a substrate.

Further, the compound of Chemical Formula 1 can be formed as an organicmaterial layer by not only a vacuum deposition method, but also asolution application method when an organic light emitting device ismanufactured. Here, the solution application method means spin coating,dip coating, doctor blading, inkjet printing, screen printing, a spraymethod, roll coating, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, thefirst electrode is a positive electrode, and the second electrode is anegative electrode.

According to another exemplary embodiment of the present specification,the first electrode is a negative electrode, and the second electrode isa positive electrode.

It is preferred that as the positive electrode material, materialshaving a high work function are usually used so as to facilitate theinjection of holes into an organic material layer. Specific examples ofthe positive electrode material which can be used in the presentinvention include: a metal such as vanadium, chromium, copper, zinc, andgold, or an alloy thereof; a metal oxide such as zinc oxide, indiumoxide, indium tin oxide (ITO), and indium zinc oxide (IZO); acombination of a metal and an oxide, such as ZnO:Al or SnO₂:Sb; aconductive polymer such as poly(3-methylthiophene),poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, andpolyaniline; and the like, but are not limited thereto.

It is preferred that as the negative electrode material, materialshaving a low work function are usually used so as to facilitate theinjection of electrons into an organic material layer. Specific examplesof the negative electrode material include: a metal such as magnesium,calcium, sodium, potassium, titanium, indium, yttrium, lithium,gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; amulti-layer structured material such as LiF/Al or LiO₂/Al and Mg/Ag; andthe like, but are not limited thereto.

The hole injection layer is a layer which injects holes from anelectrode, and a hole injection material is preferably a compound whichhas a capability of transporting holes and thus has an effect ofinjecting holes at a positive electrode and an excellent effect ofinjecting holes into a light emitting layer or a light emittingmaterial, prevents excitons produced from the light emitting layer frommoving to an electron injection layer or an electron injection material,and is also excellent in the ability to form a thin film. The highestoccupied molecular orbital (HOMO) of the hole injection material ispreferably a value between the work function of the positive electrodematerial and the HOMO of the neighboring organic material layer.Specific examples of the hole injection material include metalporphyrin, oligothiophene, arylamine-based organic materials,hexanitrile hexaazatriphenylene-based organic materials,quinacridone-based organic materials, perylene-based organic materials,anthraquinone, polyaniline-based and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

In an exemplary embodiment of the present specification, in a holeinjection layer, an arylamine-based organic material is doped with ahexanitrilehexaaza-triphenylene-based organic material.

The hole transport layer is a layer which accepts holes from a holeinjection layer and transports the holes to a light emitting layer, anda hole transport material is suitably a material having high holemobility which can accept holes from a positive electrode or a holeinjection layer and transfer the holes to a light emitting layer.Specific examples thereof include arylamine-based organic materials,conductive polymers, block copolymers having both conjugated portionsand non-conjugated portions, and the like, but are not limited thereto.

A light emitting material for the light emitting layer is a materialwhich can emit light in a visible light region by accepting andcombining holes and electrons from a hole transport layer and anelectron transport layer, respectively, and is preferably a materialhaving high quantum efficiency for fluorescence or phosphorescence.Specific examples thereof include: 8-hydroxy-quinoline aluminumcomplexes (Alq₃); carbazole-based compounds; dimerized styryl compounds;BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-based,benzothiazole-based and benzoimidazole-based compounds;poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds;polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer can include a host material and a dopantmaterial. Examples of the host material include a fused aromatic ringderivative, or a hetero ring-containing compound, and the like. Specificexamples of the fused aromatic ring derivative include an anthracenederivative, a pyrene derivative, a naphthalene derivative, a pentacenederivative, a phenanthrene compound, a fluoranthene compound, and thelike, and examples of the hetero ring-containing compound include acarbazole derivative, a dibenzofuran derivative, a ladder-type furancompound, a pyrimidine derivative, and the like, but the examplesthereof are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, astyrylamine compound, a boron complex, a fluoranthene compound, a metalcomplex, and the like. Specifically, the aromatic amine derivative is afused aromatic ring derivative having a substituted or unsubstitutedarylamino group, and examples thereof include a pyrene, an anthracene, achrysene, a periflanthene, and the like, which have an arylamino group,and the styrylamine compound is a compound in which a substituted orunsubstituted arylamine is substituted with at least one arylvinylgroup, and one or two or more substituents selected from the groupconsisting of an aryl group, a silyl group, an alkyl group, a cycloalkylgroup, and an arylamino group is or are substituted or unsubstituted.Specific examples thereof include styrylamine, styryldiamine,styryltriamine, styryltetramine, and the like, but are not limitedthereto. Further, examples of the metal complex include an iridiumcomplex, a platinum complex, and the like, but are not limited thereto.

The electron transport layer is a layer which accepts electrons from anelectron injection layer and transports the electrons to a lightemitting layer, and an electron transporting material is suitably amaterial having high electron mobility which can proficiently acceptelectrons from a negative electrode and transfer the electrons to alight emitting layer. Specific examples thereof include: Al complexes of8-hydroxyquinoline; complexes including Alq₃; organic radical compounds;hydroxyflavone-metal complexes; and the like, but are not limitedthereto. The electron transport layer can be used with any desiredcathode material, as used according to the related art. In particular,appropriate examples of the cathode material are a typical materialwhich has a low work function, followed by an aluminum layer or a silverlayer. Specific examples thereof include cesium, barium, calcium,ytterbium, and samarium, in each case followed by an aluminum layer or asilver layer.

The electron injection layer is a layer which injects electrons from anelectrode, and an electron injection material is preferably a compoundwhich has a capability of transporting electrons, an effect of injectingelectrons from a negative electrode, and an excellent effect ofinjecting electrons into a light emitting layer or a light emittingmaterial, prevents excitons produced from the light emitting layer frommoving to a hole injection layer, and is also excellent in the abilityto form a thin film. Specific examples thereof include fluorenone,anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole,oxadiazole, triazole, imidazole, perylenetetracarboxylic acid,fluorenylidene methane, anthrone, and the like, and derivatives thereof,metal complex compounds, nitrogen-containing 5-membered ringderivatives, and the like, but are not limited thereto.

Examples of the metal complex compounds include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum,tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc,bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato)aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato) gallium, and thelike, but are not limited thereto.

In an exemplary embodiment of the present specification, an electroninjection and transport layer includes an alkali metal complex compound.

The electron blocking layer is a layer which can improve the servicelife and efficiency of a device by preventing electrons injected from anelectron injection layer from passing through a light emitting layer andentering a hole injection layer. The publicly-known material can be usedwithout limitation, and can be formed between a light emitting layer anda hole injection layer, or between a light emitting layer and a layerwhich simultaneously injects and transports holes.

The hole blocking layer is a layer which blocks holes from reaching anegative electrode, and can be generally formed under the sameconditions as those of the electron injection layer. Specific examplesthereof include an oxadiazole derivative or a triazole derivative, aphenanthroline derivative, an aluminum complex, and the like, but arenot limited thereto.

The organic light emitting device according to the present specificationcan be a top emission type, a bottom emission type, or a dual emissiontype according to the materials to be used.

EXAMPLES

Hereinafter, the present invention will be described in detail withreference to Examples, Comparative Examples, and the like forspecifically describing the present specification. However, the Examplesand the Comparative Examples according to the present specification canbe modified in various forms, and it is not interpreted that the scopeof the present specification is limited to the Examples and theComparative Examples described below in detail. The Examples and theComparative Examples of the present specification are provided to morecompletely explain the present specification to a person with ordinaryskill in the art.

Synthesis Examples Synthesis of Intermediate 1. Synthesis ofIntermediate of General Reaction

1) Preparation of Compound a-2

200.0 g (1.0 eq) of 7-chloronaphthalen-2-amine, 443.25 g (1.0 eq) of1-bromo-4-chloro-2-iodobenzene, 201.3 g (1.5 eq) of NaOtBu, 3.13 g (0.01eq) of Pd(OAc)₂, and 8.08 g (0.01 eq) of Xantphos were dissolved in 4 Lof 1,4-dioxane, and the resulting solution was stirred under reflux.After 3 hours, when the reaction was terminated, the solvent was removedby reducing pressure. Thereafter, the resulting product was completelydissolved in ethyl acetate, the resulting solution was washed withwater, and 70% of the solvent was removed again by reducing thepressure. Again, hexane was put thereinto in a reflux state, andcrystals were precipitated, cooled, and then filtered. The resultingproduct was subjected to column chromatography to obtain 283.41 g (yield61%) of Compound a-2. [M+H]=333

2) Preparation of Compound a-1

283.41 g (1.0 eq) of Compound a-2, 3.90 g (0.01 eq) of Pd(t-Bu₃P)₂, and212.21 g (2.50 eq) of K₂CO₃ were added to 2 L of dimethylacetamide, andthe resulting mixture was stirred under reflux. After 3 hours, crystalswere precipitated by pouring the reactant into water, and filtered.After the filtered solid was completely dissolved in1,2-dichlorobenzene, the resulting solution was washed with water,crystals were precipitated by concentrating the solution in which theproduct was dissolved, under reduced pressure, cooled, and thenfiltered. The product was purified by column chromatography to obtain74.97 g (yield 39%) of Compound a-1 3,8-dichloro-5H-benzo[b]carbazole.[M+H]=252

2. Synthesis of Intermediate of General Reaction Scheme 3

1) Synthesis of Intermediate A-2

After 40 g of 2-bromo-7-methoxynaphthalene, 40 g of Intermediate A-1,110 g of cesium carbonate, and 0.86 g of)[bis(tri(tert-butyl)phosphine)palladium(0)] Pd(PtBu₃)₂ were added to 1.2L of xylene under a nitrogen atmosphere, the resulting mixture washeated at 150° C. and stirred for 5 hours. After the reaction wasterminated, the reaction solution was cooled to room temperature,aliquoted by adding water and aq. NH₄Cl thereto, and then filteredthrough a treatment with MgSO₄ (anhydrous). The filtered solution wasdistilled off under reduced pressure and purified with recrystallization(toluene/acetonitrile) to obtain 52 g of Intermediate A-2. [M+H]=388

2) Synthesis of Intermediate A-3

After 45 g of Intermediate A-2, 22 g of sodium tert-butoxide, and 1.2 gof [bis(tri(tert-) butyl)phosphine)palladium(0)] Pd(PtBu₃)₂ were addedto 500 mL of dimethylacetamide under a nitrogen atmosphere, theresulting mixture was heated at 120° C. and stirred for 10 hours. Afterthe reaction was terminated, the reaction solution was cooled to roomtemperature, aliquoted by adding water and aq. NH₄Cl thereto, and thenfiltered through a treatment with MgSO₄ (anhydrous). The filteredsolution was distilled off under reduced pressure and purified withrecrystallization (toluene/hexane) to obtain 22 g of Intermediate A-3.[M+H]=352

3) Synthesis of Intermediate A-5

After 20 g of Intermediate A-3 and 23 g of aluminum chloride were addedto 200 mL of chlorobenzene under a nitrogen atmosphere, the resultingmixture was heated at 130° C. and stirred for 8 hours. After thereaction was terminated, the reaction solution was cooled to roomtemperature, aliquoted by adding water and ethyl acetate thereto, andthen filtered through a treatment with MgSO₄ (anhydrous). The filteredsolution was distilled off under reduced pressure and purified withrecrystallization (ethyl acetate/hexane) to obtain 15 g of IntermediateA-4.

After 300 mL of dimethylformamide was added to 15 g of Intermediate A-4and 32 g of potassium carbonate, 17 mL of nonaflyl fluoride(nonafluorobutane-sulfonyl fluoride) was added dropwise thereto at roomtemperature. After the reaction was terminated by stirring the resultingmixture for 5 hours, the reaction solution was filtered. The filteredsolution was aliquoted by adding water and ethyl acetate thereto, andthen filtered with a treatment with MgSO₄ (anhydrous). The filteredsolution was distilled off under reduced pressure and purified withrecrystallization (toluene/hexane) to obtain 30 g of Intermediate A-5.

3. Synthesis of Compound Synthesis Example 1

10.0 g (1.0 eq) of Compound 1-1, 19.52 g (2.2 eq) ofdi([1,1′-biphenyl]-4-yl)amine, 0.14 g (0.01 eq) of Pd(t-Bu₃P)₂, and 6.63g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and the resultingmixture was stirred under reflux. After 2 hours, when the reaction wasterminated, the solvent was removed by reducing pressure. Thereafter,the resulting product was completely dissolved in CHCl₃, the resultingsolution was washed with water, and approximately 50% of the solvent wasremoved again by reducing pressure. Again, ethyl acetate was putthereinto in a reflux state, and crystals were precipitated, cooled, andthen filtered. The resulting product was subjected to columnchromatography to obtain 16.72 g (yield 65%) of Compound 1. [M+H]=933

Synthesis Example 2

10.0 g (1.0 eq) of Compound 2-1, 12.69 g (2.2 eq) ofN-phenyl-4-(trimethylsilyl)aniline, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂, and5.74 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 12.57 g (yield 61%) of Compound 2. [M+H]=829

Synthesis Example 3

10.0 g (1.0 eq) of Compound 3-1, 12.74 g (2.2 eq) ofN-(phenyl-d5)naphthalen-1-amine, 0.13 g (0.01 eq) of Pd(t-Bu₃P)₂, and6.20 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 13.20 g (yield 67%) of Compound 3. [M+H]=763

Synthesis Example 4

10.0 g (1.0 eq) of Compound 4-1, 15.22 g (2.2 eq) ofN-(3,5-dimethylphenyl)dibenzo[b,d]thiophen-4-amine, 0.11 g (0.01 eq) ofPd(t-Bu₃P)₂, and 5.48 g (2.5 eq) of NaOtBu were added to 250 ml ofxylene, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 14.19 g (yield 64%) ofCompound 4. [M+H]=973

Synthesis Example 5

10.0 g (1.0 eq) of Compound 5-1, 15.70 g (2.2 eq) ofN-(4-fluorophenyl)-6-(methyl-d3)dibenzo[b,d]furan-4-amine, 0.12 g (0.01eq) of Pd(t-Bu₃P)₂, and 5.82 g (2.5 eq) of NaOtBu were added to 250 mlof xylene, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 13.50 g (yield 60%) ofCompound 5. [M+H]=929

Synthesis Example 6

10 g (1.0 eq) of Compound 6-1, 12.77 g (2.2 eq) of4-(tert-butyl)-N-(p-tolyl)aniline, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂, and5.82 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 12.89 g (yield 65%) of Compound 6. [M+H]=819

Synthesis Example 7

10.0 g (1.0 eq) of Compound 7-1, 17.21 g (2.2 eq) ofN-(4-isopropylphenyl)-[1,1′-biphenyl]-4-amine, 0.14 g (0.01 eq) ofPd(t-Bu₃P)₂, and 6.54 g (2.5 eq) of NaOtBu were added to 250 ml ofxylene, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 15.38 g (yield 65%) ofCompound 7. [M+H]=870

Synthesis Example 8

10.0 g (1.0 eq) of Compound 8-1, 20.48 g (2.2 eq) ofN-([1,1′-biphenyl]-3-yl)dibenzo[b,d]furan-2-amine, 0.14 g (0.01 eq) ofPd(t-Bu₃P)₂, and 6.67 g (2.5 eq) of NaOtBu were added to 250 ml ofxylene, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 17.28 g (yield 65%) ofCompound 8. [M+H]=959

Synthesis Example 9

1.0 g (1.0 eq) of Compound 9-1, 11.15 g (2.2 eq) ofN-phenylnaphthalen-2-amine, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂, and 5.56 g(2.5 eq) of NaOtBu were added to 250 ml of xylene, and the resultingmixture was stirred under reflux. After 2 hours, when the reaction wasterminated, the solvent was removed by reducing pressure. Thereafter,the resulting product was completely dissolved in CHCl₃, the resultingsolution was washed with water, and approximately 50% of the solvent wasremoved again by reducing pressure. Again, ethyl acetate was putthereinto in a reflux state, and crystals were precipitated, cooled, andthen filtered. The resulting product was subjected to columnchromatography to obtain 12.33 g (yield 61%) of Compound 9. [M+H]=875

Synthesis Example 10

10.0 g (1.0 eq) of Compound 10-1, 13.32 g (2.2 eq) ofN-(phenyl-d5)dibenzo[b,d]furan-4-amine, 0.14 g (0.01 eq) of Pd(t-Bu₃P)₂,and 5.50 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 12.88 g (yield 63%) of Compound 10. [M+H]=893

Synthesis Example 11

10.0 g (1.0 eq) of Compound 11-1, 14.76 g (2.2 eq) ofN-phenyldibenzo[b,d]thiophen-1-amine, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂,and 5.85 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 14.07g (yield 65%) of Compound 11. [M+H]=889

Synthesis Example 12

10.0 g (1.0 eq) of Compound 12-1, 15.30 g (2.2 eq) of9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 0.12 g (0.01 eq) ofPd(t-Bu₃P)₂, and 5.86 g (2.5 eq) of NaOtBu were added to 250 ml ofxylene, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 13.50 g (yield 61%) ofCompound 12. [M+H]=909

Synthesis Example 13

10.0 g (1.0 eq) of Compound 13-1, 13.36 g (2.2 eq) ofN-(4-methoxyphenyl)naphthalen-2-amine, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂,and 5.86 g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 13.04 g (yield 64%) of Compound 13. [M+H]=837

Synthesis Example 14

10.0 g (1.0 eq) of Compound 14-1, 11.00 g (2.2 eq) of3-(o-tolylamino)benzonitrile, 0.12 g (0.01 eq) of Pd(t-Bu₃P)₂, and 5.77g (2.5 eq) of NaOtBu were added to 250 ml of xylene, and the resultingmixture was stirred under reflux. After 2 hours, when the reaction wasterminated, the solvent was removed by reducing pressure. Thereafter,the resulting product was completely dissolved in CHCl₃, the resultingsolution was washed with water, and approximately 50% of the solvent wasremoved again by reducing pressure. Again, ethyl acetate was putthereinto in a reflux state, and crystals were precipitated, cooled, andthen filtered. The resulting product was subjected to columnchromatography to obtain 11.13 g (yield 61%) of Compound 14. [M+H]=760

Synthesis Example 15

17.18 g (1.0 eq) of Compound 15-1, 5.79 g (2.2 eq) ofbis(4-(tert-butyl)phenyl)amine, 0.14 g (0.01 eq) of Pd(t-Bu₃P)₂, and18.34 g (2.5 eq) of K₃PO₄ were added to 250 ml of dioxane, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 14.45 g (yield 67%) of Compound 15. [M+H]=891

Synthesis Example 16

10.0 g (1.0 eq) of Compound 16-1, 22.13 g (2.2 eq) ofN-(4-(tert-butyl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, 0.17 g (0.01eq) of Pd(t-Bu₃P)₂, and 15.63 g (2.5 eq) of K₃PO₄ were added to 250 mlof dioxane, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 20.14 g (yield 67%) ofCompound 16. [M+H]=1021

Synthesis Example 17

10.0 g (1.0 eq) of Compound 17-1, 16.28 g (2.2 eq) of2-methyl-N-(4-(trifluoromethyl)phenyl)aniline, 0.15 g (0.01 eq) ofPd(t-Bu₃P)₂, and 15.63 g (2.5 eq) of K₃PO₄ were added to 250 ml ofdioxane, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 15.84 g (yield 64%) ofCompound 17. [M+H]=840

Synthesis Example 18

10.0 g (1.0 eq) of Compound 18-1, 18.23 g (2.2 eq) ofN-(3,5-difluorophenyl)-[1,1′-biphenyl]-4-amine, 0.15 g (0.01 eq) ofPd(t-Bu₃P)₂, and 15.63 g (2.5 eq) of K₃PO₄ were added to 250 ml ofdioxane, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 16.17 g (yield 61%) ofCompound 18. [M+H]=900

Synthesis Example 19

10.0 g (1.0 eq) of Compound 19-1, 19.43 g (2.2 eq) ofN-(3-(trimethylsilyl)phenyl)dibenzo[b,d] thiophen-2-amine, 0.12 g (0.01eq) of Pd(t-Bu₃P)₂, and 13.48 g (2.5 eq) of K₃PO₄ were added to 250 mlof dioxane, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 18.50 g (yield 67%) ofCompound 19. [M+H]=1087

Synthesis Example 20

10.0 g (1.0 eq) of Compound 20-1, 13.82 g (2.2 eq) ofN-phenyl-[1,1′-biphenyl]-4-amine, 0.13 g (0.01 eq) of Pd(t-Bu₃P)₂, and13.59 g (2.5 eq) of K₃PO₄ were added to 250 ml of dioxane, and theresulting mixture was stirred under reflux. After 2 hours, when thereaction was terminated, the solvent was removed by reducing pressure.Thereafter, the resulting product was completely dissolved in CHCl₃, theresulting solution was washed with water, and approximately 50% of thesolvent was removed again by reducing pressure. Again, ethyl acetate wasput thereinto in a reflux state, and crystals were precipitated, cooled,and then filtered. The resulting product was subjected to columnchromatography to obtain 13.73g (yield 61%) of Compound 20. [M+H]=880

Synthesis Example 21

10.0 g (1.0 eq) of Compound 21-1, 21.14 g (2.2 eq) ofN-([1,1′-biphenyl]-3-yl)naphthalen-2-amine, 0.16 g (0.01 eq) ofPd(t-Bu₃P)₂, and 17.26 g (2.5 eq) of K₃PO₄ were added to 250 ml ofdioxane, and the resulting mixture was stirred under reflux. After 2hours, when the reaction was terminated, the solvent was removed byreducing pressure. Thereafter, the resulting product was completelydissolved in CHCl₃, the resulting solution was washed with water, andapproximately 50% of the solvent was removed again by reducing pressure.Again, ethyl acetate was put thereinto in a reflux state, and crystalswere precipitated, cooled, and then filtered. The resulting product wassubjected to column chromatography to obtain 18.95 g (yield 65%) ofCompound 21. [M+H]=897

EXPERIMENTAL EXAMPLE Example 1

A glass substrate thinly coated with indium tin oxide (ITO) to have athickness of 1,000 Å was added to distilled water in which a detergentwas dissolved, and ultrasonically washed. In this case, a productmanufactured by the Fischer Co., was used as the detergent, anddistilled water twice filtered using a filter manufactured by MilliporeCo., was used as the distilled water. After the ITO was washed for 30minutes, ultrasonic washing was repeated twice by using distilled waterfor 10 minutes. After the washing using distilled water was completed,ultrasonic washing was conducted by using isopropyl alcohol, acetone,and methanol solvents, and the resulting product was dried and thentransported to a plasma washing machine. Furthermore, the substrate wascleaned by using an oxygen plasma for 5 minutes, and then wastransported to a vacuum deposition machine.

The following HI-1 compound was formed to have a thickness of 1,150 Å asa hole injection layer on the thus prepared transparent ITO electrode,and was p-doped with the following A-1 compound at a concentration of1.5%. The following HT-1 compound was vacuum deposited on the holeinjection layer, thereby forming a hole transport layer having a filmthickness of 800 Å. Next, the following EB-1 compound was vacuumdeposited to have a film thickness of 150 Å on the hole transport layer,thereby forming an electron blocking layer. Next, the following BH-1compound as a host and Compound 1 as a dopant were vacuum deposited at aweight ratio of 98:2 (host:dopant) on the electron blocking layer,thereby forming a blue light emitting layer having a thickness of 200 Å.The following HB-1 compound was vacuum deposited to have a filmthickness of 30 Å on the light emitting layer, thereby forming a holeblocking layer. Next, the following ET-1 compound and the following LiQcompound were vacuum deposited at a weight ratio of 2:1 on the holeblocking layer, thereby forming an electron injection and transportlayer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminumwere sequentially deposited on the electron injection and transportlayer to have a thickness of 12 Å and 1,000 Å, respectively, therebyforming a negative electrode.

In the aforementioned procedure, the deposition rate of the organicmaterial was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition ratesof lithium fluoride and aluminum of the negative electrode weremaintained at 0.3 Å/sec and at 2 Å/sec, respectively, and the degree ofvacuum during the deposition was maintained at 2×10⁻⁷ torr to 5×10⁻⁶torr, thereby manufacturing an organic light emitting device.

Examples 2 to 21

Organic light emitting devices were manufactured in the same manner asin Example 1, except that the compounds described in the following Table1 were used instead of Compound 1 in the organic light emitting devicein Example 1.

Comparative Examples 1 to 7

Organic light emitting devices were manufactured in the same manner asin Example 1, except that the compounds described in the following Table1 were used instead of Compound 1 in the organic light emitting devicein Example 1.

For the organic light emitting devices of Examples 1 to 21 andComparative Examples 1 to 7, the driving voltage, the light emittingefficiency and color coordinate were measured at a current density of 10mA/cm², and a time (LT95) for reaching a 95% value compared to theinitial luminance was measured at a current density of 20 mA/cm². Theresults are shown in the following Table 1.

TABLE 1 10 mA/cm² Driving 20 mA/cm² voltage Efficiency Service ExampleDopant (v) (cd/A) CIEy life (hr), 95% Example 1 Compound 1 4.5 5.9 0.08185 Example 2 Compound 2 4.6 6.1 0.12 189 Example 3 Compound 3 4.5 5.60.08 176 Example 4 Compound 4 4.6 5.7 0.08 177 Example 5 Compound 5 4.85.4 0.10 193 Example 6 Compound 6 4.4 5.5 0.09 205 Example 7 Compound 74.3 6.0 0.12 183 Example 8 Compound 8 4.5 6.1 0.10 194 Example 9Compound 9 4.4 5.5 0.09 171 Example 10 Compound 10 4.6 5.7 0.11 176Example 11 Compound 11 4.5 5.6 0.08 187 Example 12 Compound 12 4.7 5.70.09 177 Example 13 Compound 13 4.7 5.4 0.08 194 Example 14 Compound 144.5 6.1 0.12 203 Example 15 Compound 15 4.3 5.8 0.10 189 Example 16Compound 16 4.5 5.7 0.09 164 Example 17 Compound 17 4.7 5.8 0.11 198Example 18 Compound 18 4.6 6.0 0.12 183 Example 19 Compound 19 4.4 5.90.11 172 Example 20 Compound 20 4.8 5.5 0.09 180 Example 21 Compound 214.4 5.7 0.10 193 Comparative C-1 4.8 4.9 0.12 157 Example 1 ComparativeC-2 5.0 5.7 0.09 108 Example 2 Comparative C-3 5.0 4.1 0.17 121 Example3 Comparative C-4 5.1 4.5 0.13 83 Example 4 Comparative C-5 4.8 4.9 0.15137 Example 5 Comparative C-6 4.9 4.8 0.13 97 Example 6 Comparative C-74.6 5.0 0.16 145 Example 7

When an electric current was applied to the organic light emittingdevices manufactured in Examples 1 to 21 and Comparative Examples 1 to7, the results of Table 1 were obtained. All of the Examples and theComparative Examples exhibited blue light emission. From the results ofTable 1, it could be seen that when the compound of the presentinvention was used as a dopant of a blue light emitting layer, thedriving voltage was significantly lowered by 15% or more and theefficiency was increased by 48% or more, as compared to the materials inthe Comparative Examples, and that the service life characteristicscould be significantly improved while maintaining the high efficiency.

Example 22: Measurement of Maximum Emission Wavelength and Full Width atHalf-Maximum

The fluorescence intensity and the maximum emission peak were measuredat room temperature (300 K) by dissolving Compound 12 at a concentrationof 1 μM in toluene as a solvent to prepare a sample for measuringfluorescence, putting the sample solution into a quartz cell, and thenusing a fluorescence measurement apparatus (JASCO FP-8600 fluorescencespectrophotometer). In this case, in the fluorescence spectrum, the xaxis is the wavelength (λ, unit: nm), the y axis is the light emissiondegree, and a spread width of a peak at a height that is ½ of the heightof the maximum emission peak refers to a full width at half-maximum.

Example 23 and Comparative Examples 8 to 10

The maximum emission wavelengths and the full widths at half-maximumwere measured by using the compounds shown in the following Table 2instead of Compound 12 in Example 22, and are shown in Table 2.

TABLE 2 Solution PL Maximum Full width emission at wavelengthhalf-maximum Example Dopant (nm) (nm) Example 22 Compound 12 447 24Example 23 Compound 15 448 25 Comparative C-1 451 44 Example 8Comparative C-2 440 38 Example 9 Comparative C-3 448 52 Example 10

From Table 2, it can be seen that the full widths at half-maximum in theExamples are 30 nm or less, whereas the full widths at half-maximum inthe Comparative Examples were more than 30 nm. It can be seen that whenthe compound of Chemical Formula 1 is used as a blue emission dopant,the color purity is good due to the narrow full width at half-maximum.

1. A compound of Chemical Formula 1:

wherein in Chemical Formula 1: Ar11 to Ar15 are the same as or differentfrom each other, and are each independently is a substituted orunsubstituted aryl group or a substituted or unsubstituted heteroarylgroup, or are bonded to an adjacent substituent to form a substituted orunsubstituted ring; L and L2 to L5 are the same as or different fromeach other, and each independently is a direct bond or a substituted orunsubstituted arylene group; R1 is hydrogen, deuterium, a halogen group,a nitrile group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heteroaryl group, or is bonded to anadjacent substituent to form a substituted or unsubstituted ring; r1 isan integer from 0 to 8, and when r1 is 2 or more, the R1s are the sameas or different from each other; and n is an integer from 1 to 3, andwhen n is 2 or 3, the Ls are the same as or different from each other.2. The compound of claim 1, wherein Chemical Formula 1 is ChemicalFormula 2:

wherein in Chemical Formula 2, the definitions of Ar11 to Ar15, L, L2 toL5, R1, r1, and n are the same as defined in Chemical Formula
 1. 3. Thecompound of claim 1, wherein Chemical Formula 1 is any one of thefollowing Chemical Formulae 301 to 303:

wherein in Chemical Formulae 301 to 303: the definitions of L2 to L5 andAr11 to Ar14 are the same as defined in Chemical Formula 1; Ar21 is asubstituted or unsubstituted aryl group or a substituted orunsubstituted heteroaryl group; R21 and R22 are the same as or differentfrom each other, and are each independently hydrogen, deuterium, ahalogen group, a nitrile group, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted haloalkyl group, a substituted orunsubstituted silyl group, substituted or unsubstituted alkoxy group, asubstituted or unsubstituted cycloalkyl group, a substituted orunsubstituted aryl group or a substituted or unsubstituted heteroarylgroup; k1 and k2 are 0 or 1; and r21 and r22 are an integer from 0 to 6,wherein when r21 is 2 or more, the R21s are the same as or differentfrom each other, and when r22 is 2 or more, the R22s are the same as ordifferent from each other.
 4. The compound of claim 1, wherein Ar11 toAr14 are the same as or different from each other, and eachindependently is an aryl group which is unsubstituted or substitutedwith one substituent selected from the group consisting of deuterium, ahalogen group, a nitrile group, an alkyl group, a haloalkyl group, analkoxy group, a haloalkoxy group, a silyl group, and a cycloalkyl group,or a substituent to which two or more substituents selected from thegroup are linked; or a heteroaryl group which is unsubstituted orsubstituted with one substituent selected from the group consisting ofdeuterium, a halogen group, a nitrile group, an alkyl group, a haloalkylgroup, an alkoxy group, a haloalkoxy group, a silyl group, and acycloalkyl group, or a substituent to which two or more substituentsselected from the group are linked.
 5. The compound of claim 1, wherein-(L)n-Ar15 in Formula 1 is a phenyl group which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, an alkylgroup which is unsubstituted or substituted with deuterium, an alkoxygroup, or a silyl group; or a biphenyl group which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, an alkylgroup which is unsubstituted or substituted with deuterium, an alkoxygroup, or a silyl group.
 6. The compound of claim 1, wherein Ar15 isbonded to adjacent R1 to form a benzene ring which is unsubstituted orsubstituted with deuterium, a halogen group, a nitrile group, a methylgroup, an isopropyl group, a t-butyl group, a methoxy group, CD₃, aphenyl group, a phenyl group which is substituted with deuterium, aphenyl group which is substituted with a halogen group, a phenyl groupwhich is substituted with a nitrile group, or a phenyl group which issubstituted with a methyl group; or a naphthalene ring.
 7. The compoundof claim 1, wherein the compound of Chemical Formula 1 is any one of thefollowing compounds:


8. An organic light emitting device comprising: a first electrode; asecond electrode provided to face the first electrode; and an organicmaterial layer having one or two or more layers provided between thefirst electrode and the second electrode, wherein one or more layers ofthe organic material layer comprise the compound of claim
 1. 9. Theorganic light emitting device of claim 8, wherein the organic materiallayer comprises a light emitting layer, and the light emitting layercomprises the compound.
 10. The organic light emitting device of claim8, wherein the organic material layer comprises a light emitting layer,and the light emitting layer comprises the compound as a dopant of thelight emitting layer.
 11. The organic light emitting device of claim 8,wherein the organic material layer comprises a light emitting layer, andthe light emitting layer comprises the compound and a compound ofChemical Formula H:

wherein in Chemical Formula H: L21 and L22 are the same as or differentfrom each other, and are each independently a direct bond, a substitutedor unsubstituted arylene group, or a substituted or unsubstitutedheteroarylene group, R31 to R38 are the same as or different from eachother, and are each independently hydrogen, deuterium, a substituted orunsubstituted alkyl group, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted silyl group, a substituted orunsubstituted phosphine oxide group, a substituted or unsubstituted arylgroup, or a substituted or unsubstituted heteroaryl group, and Ar101 andAr102 are the same as or different from each other, and eachindependently is a substituted or unsubstituted aryl group or asubstituted or unsubstituted heteroaryl group.